“I ain’t as good as I once was, but I’m as good once, as I ever was.” A man who knows a thing or two about writing chart-topping hits, Toby Keith is a singer, songwriter, actor, and record producer who caught his first big break in the early 1990s after a brief career in the oil fields and on the football field. Writing his first mega hit, “Should’ve Been a Cowboy,” in 1993, Keith’s popularity skyrocketed as the song became the most-played of the decade and paved the way for future success with albums like Pull My Chain, Unleashed, Shock’n Ya’ll, Big Dog Daddy, and Hope on the Rocks. Still churning out top-charting singles like “Beer for My Horses,” “As Good As I Once Was” and “Red Solo Cup,” let’s take a look at the Oklahoma native’s career from the oil field to the football field, stage and beyond!

Toby Keith Covel was born on July 8, 1961 in Clinton, Oklahoma to Carolyn Joan and Hubert K. Covel, Jr. When Keith was still a child, the family lived in Fort Smith, Arkansas where Keith spent most of his free time with his grandmother who owned Billie Garner’s Supper Club. It was at the club that Keith got his first taste of music and soon started taking the stage to play with the band. At only eight years old, he received his first guitar and continued practicing as the family returned to Oklahoma and settled down in the small town of Moore.

Keith attended Moore High School where he played defensive end on the football team. After graduation, he briefly considered a career in pro football before he took a job working in the oil fields. Eventually working his way up the ladder to become an operations manager by the age of 20, Keith found time to pursue his passion for music and joined friends Keith Cory, Scott Webb, David Vowell, and Danny Smith to form the Easy Money Band. The group continued to play at local bars until the oil industry experienced a drastic decline in 1982 and Keith lost his job. This time, he returned to football and played defensive end for the semi-pro Oklahoma City Drillers and spent his evenings playing with his band in honkytonks across Texas, Oklahoma, and Kansas.

With the band enjoying modest success, Keith hedged his bets and headed to Nashville, Tennessee in the early 1990s where he played on Music Row and shared copies of the band’s demo tape with every label he could find. Hoping to sign a deal by his 30th birthday, he faced rejection after rejection as he made plans to return to Oklahoma. Coincidentally, on the flight home, Keith handed out one of his demo tapes to a flight attendant who liked what she heard and gave the demo tape to another friend, Mercury Records executive Harold Shedd. Instantly drawn to Keith’s vocals, Shedd traveled to Oklahoma to see Keith perform live and, after the gig, offered him a recording contract.

During this time, Keith was still playing in honkytonks and was in Dodge City, Kansas when he had an idea for a song. “A guy said to another guy, ‘In all honesty, you should’ve been a cowboy’ when a girl didn’t dance with him in his hunting clothes,” Keith recalled. “And I thought, ‘Man, that sounds like a song idea,’ and it was all over me. I went back, and we were all two hunters to a room, and my roommate was Freddie Cortez… he used to own Chastain’s and a bunch of country bars in town. Freddie went to sleep, and I didn’t want to wake him ‘cause he was hateful when you’d wake him up. I went in the bathroom, shut the door, wrote it down, and put it in my bag and went hunting the next day. Came home, revisited it, and said, ‘I’m gonna record this song.”

Doing exactly that, “Should’ve Been a Cowboy” became Keith’s debut single in 1993 and climbed to the top of the US Billboard Hot Country chart. It led his self-titled debut album and was ranked as the decade’s most played single as Keith followed up with “A Little Less Talk and a Lot More Action” and “Wish I Didn’t Know Now.” For Keith, “Should’ve Been a Cowboy” defined his early career and his path to greater success. “It’s like my pick of the littler as far as how important it was to changing my life—and a lot of people around me,” he said.

Keith went on tour with Shania Twain and John Brannen before signing on with Polydor Records to release his second album, Boomtown, in 1994. Once again, the album was a massive success with top 10 singles like “Who’s That Man” and “You Ain’t Much Fun.” By the mid-1990s, he jumped to a third label, the short-lived A&M Records, and released his third album, Blue Moon. After a corporate merger forced him back to Mercury in 1997, he released his fourth album, Dream Walkin’, and finished up his stint with Mercury with his Greatest Hits Volume One album in 1998.

Between 1998 and 2005, Keith recorded under DreamWorks and reinvented himself as a bad boy country star with the chart-topping single, “How Do You Like Me Now?” The single became the most popular country song of the year in 2000 and headlined Keith’s next album by the same name. From there, Keith released Pull My Chain in 2001, Unleashed in 2002, and Shock’n Y’all in 2003 with hit singles like “Courtesy of the Red, White, & Blue (The Angry American),” “Who’s Your Daddy?” and “Beer for My Horses.”

Following the closure of DreamWorks Records in 2005, Keith created his own record label—Show Dog Nashville—and released his next 10 albums: White Trash with Money (2006), Big Dog Daddy (2007), That Don’t Make Me a Bad Guy (2008), American Ride (2009), Bullets in the Gun (2010), Clancy’s Tavern (2011), Hope on the Rocks (2012), Drinks After Work (2013), 35 MPH Town (2015), and The Bus Songs (2017). Amid releasing these chart-topping albums, Keith facilitated a merger with Universal South Records and renamed his label, Show Dog-Universal Music.

With Keith’s growing success as a country singer, he extended his reach and ventured into acting with his debut in the 2006 musical drama, Broken Bridges. Three years later, he joined Rodney Carrington in Beer for My Horses and appeared opposite former Arkansas Governor Mike Huckabee on Fox’s Huckabee series in 2011. During this time, he also ventured into the restaurant business and opened Toby Keith’s I Love This Bar & Grill in Oklahoma City, Oklahoma. The restaurant has been such a huge success that he’s opened franchises across his native state as well as in New York, Arizona, Las Vegas, Massachusetts, Ohio, Virginia, Colorado, and Pennsylvania.

Made In America: Life Today

Over the last two decades, Keith has become more and more political and patriotic with his lyrics especially as he travels the world performing for soldiers on or near the front lines. “My father was a soldier,” Keith said. “He taught his kids to respect veterans. It’s that respect and the thank-you that we have a military that’s in place and ready to defend our nation, our freedom.” Of course, it’s those same political lyrics and his patriotism that often leave him in the media’s crosshairs especially after his public feud with the Dixie Chicks over his single, “Courtesy of the Red, White, & Blue” in 2003.

While the feud has since been resolved, Keith says he’s more focused on just being himself, making music for his devoted fans, and raising money through his annual Toby Keith & Friends Golf Classic. In 2018, he launched the Toby Keith Should’ve Been a Cowboy Tour XXV, which pays homage to his first hit single from 1993, and gives fans even more of what they want from his 61 chart-topping singles and over 40 million in album sales. “I’m giving the song its due… I’ve never played a show that I didn’t play that song,” Keith says. As for his philanthropy, Keith recently hosted the 15th Annual Toby Keith & Friends Golf Classic, which he started to fill a void in his community. “Fifteen years. I actually have some big donors and celebrities… they’ve been to all 15. It’s pretty crazy,” Keith says of the event’s ongoing success. “it’s really hard to be that dedicated to show up 15 years in a row. It just shows that we had a voice in our community and I was called upon in my heart to go fill that void and the community rallied behind me.”

Beyond the golf tournament’s success as well as his own on the stage, the 56-year-old Keith enjoys looking back on his career especially in comparison to today’s country music. “What’s crazy about it is that when we were coming out, the old-timers were griping at us, saying we weren’t country enough,” he says. “But, you compare it to country music today and my album is almost hillbilly sounding.”